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Published version

Publication date

2024-10-04

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cc-by (c) Duran, Jordi et al., 2024
Please use this identifier to cite or link to this item: https://hdl.handle.net/2445/222731

Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates

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https://doi.org/10.1021/acs.orglett.4c03242

Abstract

Herein we describe the organocatalytic asymmetric allylic benzylborylation of allyl fluorides with α-silyl benzylboronic esters. The catalytic protocol leverages the singular features of fluoride as an unconventional leaving group, enabling the catalytic generation of reactive α-boryl carbanion species through desilylative activation. It allows the construction of a wide set of homoallylic benzylated organoboronates bearing two contiguous stereocenters. The chiral boronate installed in the products serves as a synthetic lynchpin to construct complex chemical architectures in a stereospecific manner.

Subject

Compostos orgànics, Anions, Estructura molecular

Subject (English)

Organic compounds, Anions, Molecular structure

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Articles publicats en revistes (Química Inorgànica i Orgànica)

Citation

DURAN, Jordi, et al. Organocatalytic Asymmetric Allylic Benzylborylation via Fluoride-Assisted Catalytic Generation of α-Boryl Carbanionic Intermediates. Organic Letters. 2024. Vol. 26, num. 39, pags. 8394-8399. ISSN 1523-7060. [consulted: 12 of June of 2026]. Available at: https://hdl.handle.net/2445/222731

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